MOLECULES
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2023
·Vol. 28
·期 11
·4503
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IF 4.6
Lili Shi,Ziyu Cui,Wei Liu
β-carbolines (harman and norharman) are potentially mutagenic and have been reported in some vegetable oils. Sesame seed oil is obtained from roasted sesame seeds. During sesame oil processing, roasting is the key procedure to aroma enhancement, in which β-carbolines are produced. Pressed sesame seed oils cover most market share, while leaching solvents are used to extract oils from the pressed sesame cake to improve the utilization of the raw materials. β-carbolines are nonpolar heterocyclic aromatic amines with good solubility in leaching solvents (n-hexane); therefore, the β-carbolines in sesame cake migrated to the leaching sesame seed oil. The refining procedures are indispensable for leaching sesame seed oil, in which some small molecules can be reduced. Thus, the critical aim is to evaluate the changes in β-carboline content during the refining of leaching sesame seed oil and the key process steps for the removal of β-carbolines. In this work, the levels of β-carbolines (harman and norharman) in sesame seed oil during chemical refining processes (degumming, deacidification, bleaching and deodorization) have been determined using solid phase extraction and high performance liquid chromatography-mass spectrometry (LC-MS). The results indicated that in the entire refining process, the levels of total β-carbolines greatly decreased, and the adsorption decolorization was the most effective process in reducing β-carbolines, which might be related to the adsorbent used in the decolorization process. In addition, the effects of adsorbent type, adsorbent dosage and blended adsorbent on β-carbolines in sesame seed oil during the decolorization process were investigated. It was concluded that oil refining can not only improve the quality of sesame seed oil, but also reduce most of the harmful β-carbolines.Keywords:adsorbent;β-carbolines;harman;norharman;sesame seed oil
研究领域:
食品科学
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化学工程
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2021
·
IF 5.279
Teng Hui,Yanlei Li,Ruixia Chen,Xiaoyue Yang,Huan Liu,Zhenyu Wang,Dequan Zhang
The aim of this study was to investigate the formation rules of 1-methyl-6-phenylimidazo[4,5-b]-pyridine (PhIP), 1-methyl-9H-pyrido[3,4-b]-indole (Harman), and 9H-pyrido[3,4-b]-indole (Norharman) in chemical model systems containing epicatechin under various reaction conditions and establish their prediction models. The results indicated that at 100–200 °C and pH 5.5–7.5 for 10–90 min, epicatechin inhibited the formation of PhIP, Harman, and Norharman by 32–100, 1–93, and 5–98%, respectively. The exponential growth equation in the growth model with R2 of 0.986–0.997, the second-order equation in the polynomial model with R2 of 0.900–0.949, and the trigonometric function equation in the Fourier model with R2 of 0.513–0.926 were well fitted for the formation of PhIP, Harman, and Norharman at various temperatures, times, and pHs, respectively. The calibration set (R2c) and the prediction set (R2p) of the optimal partial least squares regression prediction model was 0.74 and 0.70 for PhIP, 0.75 and 0.70 for Harman, and 0.90 and 0.91 for Norharman, respectively. The results provide theoretical support to develop technologies or equipment for the real-time synchronous monitoring of PhIP, Harman, and Norharman during meat processing.
研究领域:
食品化学
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分析化学
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食品科学
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DOI
PubMed
高影响因子
FOOD RESEARCH INTERNATIONAL
·
2023
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IF 8.1
Yuanyuan Wang,Maofeng Dong,Limin Guo,Yamin Zhu,Qingqing Jiang,Jianbo Xiao,Mingfu Wang,Yueliang Zhao
Harman and norharman were the most abundant β-carboline-type heterocyclic amines (HCAs) detected in various foodstuffs. Unsaturated fatty acids in foods may undergo rapid oxidative deterioration during transportation, storage and heat treatment, forming reactive carbonyl species (RCS). This work studied the effects of acrolein, a highly reactive RCS, on the formation of harman and norharman in the tryptophan model system. Results showed that 0.005, 0.01, 0.015, 0.02, 0.05, 0.1 and 0.2 mmol of acrolein led to harman production increased by 528 %, 752 %, 981 %, 1172 %, 1375 %, 1288 % and 768 % respectively, and led to norharman formation increased by 116 %, 129 %, 152 %, 169 %, and 197 %, 185 % and 157 %, respectively. Furthermore, acrolein addition reduced the residue of tryptophan (up to 63.19 %), but increased the level of the intermediates including formaldehyde (up to 352 %), acetaldehyde (up to 491 %), (1S,3S)-1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (MTCA, up to 1936 %), and 1,2,3,4-tetrahydro-β-carboline-3-carboxylicacid (THCA, up to 2142 %) in the tryptophan model system. Acrolein might react with tryptophan, harman and norharman to eliminate them directly. These data suggested that acrolein may contribute to harman and norharman formation through participating in the above complex chemical reactions. In addition, the content of harman and norharman produced in roast beef patties made of minced beef oxidized for 2, 4, 6, 8, and 10 days increased by 118 %, 188 %, 267 %, 137 %, and 48 %, respectively, and led to norharman formation increased by 140 %, 132 %, 90 %, 86 %, and 74 %, respectively compared with those made of fresh minced beef, which further illustrated that lipid oxidation products potentially contributed to harman and norharman formation.
研究领域:
食品科学
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化学毒理学
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营养学
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DOI
PubMed
高影响因子
FOOD CHEMISTRY
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2024
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IF 8.5
Haolin Zhang,Xiaomei Lv,Weiming Su,Bing-Huei Chen,Yu-Wen Lai,Ruiwei Xie,Qiuyi Lin,Lei Chen,Hui Cao
The prevention and control of heterocyclic aromatic amines (HAA) formation to mitigate of potential risks to humans, can be achieved by targeting their precursors. In this study, the detailed roles of individual and excess component (20 common α-amino acids, creatine, creatinine, and glucose) on HAA formation in roasted beef patties were examined using UPLC-MS/MS. The results confirmed the reported classical precursors of HAAs. Some components regulated the competitive production of Norharman and Harman. Glycine (Gly) and glucose favored Norharman formation, while cysteine (Cys) and phenylalanine (Phe) for Harman. Serine (Ser) and threonine (Thr) were identified as potential precursors for IQx-type HAAs. Interestingly, methionine (Met), Gly, Thr, Cys, alanine (Ala), and Ser were revealed as more targeted underlying precursors for 1,6-DMIP and 1,5,6-TMIP, and the formation mechanism was inferred. Furthermore, Pro, Leu, His, Ile, Lys and Asp were considered as great inhibitors for HAAs.
研究领域:
食品科学
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分析化学
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毒理学
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产品关联
DOI
PubMed
高影响因子
FOOD HYDROCOLLOIDS
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2022
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IF 11.504
Lang Zhang,Xiufang Xia,Fangda Sun,Haotian Liu,Qian Chen,Baohua Kong
This study aims to investigate the inhibitory effects of hydrocolloids on heterocyclic aromatic amine (HAA) formation in chemical model systems and smoked chicken drumsticks. In chemical model systems I and II, xanthan gum (XG) and carboxymethyl cellulose sodium (CMC-Na) effectively inhibited the 2-amino-1-methyl-6-phenylimidazo[4,5- b ]pyridine (PhIP), 1-methyl-9H-pyrido[3,4- b ]indole (Harman), and 9H-pyrido[3,4- b ]indole (Norharman) formation in comparison with the control sample ( P < 0.05). Arabic gum (AG) inhibited the PhIP and Harman formation ( P < 0.05), but its inhibitory action against Norharman formation was not significant ( P > 0.05). Further mechanism investigation of chemical model system I showed that the formation of PhIP was mainly inhibited via trapping phenylalanine and creatinine by glyoxal and methyglyoxal. A mechanistic investigation of chemical model system II suggested the inhibition of Harman and Norharman formation by XG and CMC-Na could be through trapping tryptophan by glyoxal and methyglyoxal. In smoked chicken drumsticks, CMC-Na had a dose-dependent inhibitory effect against the PhIP, Harman, and Norharman formation in comparison with the control sample ( P < 0.05), and 2.0% CMC-Na had the highest inhibitory rates of 45.83%, 21.82%, and 30.92%, respectively. Moreover, CMC-Na effectively inhibited the formation of PhIP, Harman, and Norharman precursors and intermediates in smoked chicken drumsticks, which further confirmed the above inhibition mechanism of CMC-Na. These results could provide an effective approach to reduce HAA formation in smoked meat products by incorporating hydrocolloids.
研究领域:
食品科学
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化学
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毒理学
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DOI
高影响因子
Frontiers in Microbiology
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2022
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IF 6.064
Huo Jinxi,Sun Yuqing,Pan Meiliang,Ma Huanyan,Lin Tianbao,Lv Zhiqiang,Li Yougui,Zhong Shi
Sanghuangprous vaninii is a wood-inhabiting fungus, and its mycelium and fruiting body show excellent medicinal values. Mulberry is one of the major hosts of S. vaninii, however, the mechanism of mulberry affecting the growth of S. vaninii has not been reported. In the present study, a mulberry-inhabiting strain of S. vaninii was selected to explore the effects of mulberry branch extracts (MBE) on the growth of the strain. Results showed that MBE could significantly promote the growth of S. vaninii mycelium at the concentration of 0.2 g/l. After 16 days of liquid culture, the dry weight of mycelium in 0.2 g/l MBE medium was higher by three times compared with that in the control. The non-targeted metabonomic analysis of the culture medium at different culture times and concentrations was conducted to find the key components in MBE that promoted the growth of S. vaninii mycelium. Under the different concentrations of MBE culture for 10 and 16 days, 22 shared differential metabolites were identified. Next, in accordance with the peak value trend of these metabolites, HPLC–MS and liquid culture validation, four components derived from MBE (i.e., scopoletin, kynurenic acid, 3,5-dihydroxybenzoic acid and 2,4-dihydroxybenzoic acid) could significantly increase the growth rate of mycelium at the concentration of 2 mg/l. Transcriptomic and qRT-PCR analyzes showed that MBE could upregulate hydrolase-related genes, such as serine–glycine–asparaginate–histidine (SGNH) hydrolase, alpha-amylase, poly-beta-hydroxybutyrate (PHB) depolymerase, glycosyl hydrolase family 61, cerato-platanin protein and Fet3, which might enhance the nutrient absorption ability of S. vaninii. Importantly, MBE could significantly increase the content of harmine, androstenedione and vesamicol, which have been reported to possess various medicinal effects. Results suggested that MBE could be an excellent additive for liquid culture of S. vaninii mycelium, and these hydrolase-related genes also provided candidate genes for improving the nutrient absorption capacity of S. vaninii.
研究领域:
真菌学
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代谢组学
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转录组学
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药理学
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DOI
PubMed
高影响因子
BIOFOULING
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2021
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IF 3.209
Huai-Zhi Luo,Jin-Wei Zhou,Bing Sun,Huan Jiang,Shi Tang,Ai-Qun Jia
Serratia marcescens NJ01, a Gram-negative bacterium, can infect tomato leaves and cause chlorosis and wilting. The present study evaluated the quorum sensing (QS) and biofilm inhibitory effects of seven carboline compounds against S. marcescens NJ01 at 20 μg ml−1, and subsequently focused the study on norharmane as this had the best inhibitory activity. Quantitative real-time polymerase chain reaction (qRT-PCR) analysis confirmed the down-regulation of QS and biofilm related genes bsmA, bsmB, fimA, fimC, flhD, pigA, pigC and shlA on exposure to norharmane. Fourier-Transform Infrared Spectroscopy (FT-IR) analysis showed a reduction in the major components of the exopolysaccharide (EPS) matrix such as nucleic acids, proteins and fatty acids, which are involved in forming the tertiary structure of biofilms. Norharmane exposure also enhanced the susceptibility of the biofilm to ofloxacin. Hence, norharmane has the potential for use as an antibiotic adjuvant to enhance the efficacy of conventional antibiotics to reduce pathogenic bacterial infections.
研究领域:
微生物学
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药理学
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植物病理学
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DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）